Protonation of nucleobases in single- and double-stranded DNA

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F18%3A00103378" target="_blank" >RIV/00216224:14740/18:00103378 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/cbic.201800310" target="_blank" >http://dx.doi.org/10.1002/cbic.201800310</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cbic.201800310" target="_blank" >10.1002/cbic.201800310</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Protonation of nucleobases in single- and double-stranded DNA

Popis výsledku v původním jazyce

Single-stranded model oligodeoxyribonucleotides containing a single protonable base: cytosine, adenine, guanine, or 5-methylcytosine, centrally located in a background of non-protonable thymines were acid titrated in aqueous solution, with UV-monitoring. The basicity of the central base was shown to depend on the type of the central base and its nearest neighbours and to rise with increasing oligonucleotide length and decreasing ionic strength of the solution. More complex model oligonucleotides containing a centrally located 5-methylcytosine base were comparatively evaluated in single-stranded and double-stranded form, by UV-spectroscopy and high-field NMR. Compared to the single-stranded case, the N3-protonation of the 5-methylcytosine moiety in the double-stranded case occurred at much lower pH, where the duplex already suffered general dissociation. The central guanine:5-methylcytosine base pair remained intact up to this point, possibly due to an unusual alternative protonation on O2 of the 5-methylcytosine moiety already taking place at neutral or weakly basic pH, as indicated by UV spectroscopy, suggesting that in double-stranded DNA, 5-methylcytosine sites may be protonated to a significant extent under physiological conditions.

Název v anglickém jazyce

Protonation of nucleobases in single- and double-stranded DNA

Popis výsledku anglicky

Single-stranded model oligodeoxyribonucleotides containing a single protonable base: cytosine, adenine, guanine, or 5-methylcytosine, centrally located in a background of non-protonable thymines were acid titrated in aqueous solution, with UV-monitoring. The basicity of the central base was shown to depend on the type of the central base and its nearest neighbours and to rise with increasing oligonucleotide length and decreasing ionic strength of the solution. More complex model oligonucleotides containing a centrally located 5-methylcytosine base were comparatively evaluated in single-stranded and double-stranded form, by UV-spectroscopy and high-field NMR. Compared to the single-stranded case, the N3-protonation of the 5-methylcytosine moiety in the double-stranded case occurred at much lower pH, where the duplex already suffered general dissociation. The central guanine:5-methylcytosine base pair remained intact up to this point, possibly due to an unusual alternative protonation on O2 of the 5-methylcytosine moiety already taking place at neutral or weakly basic pH, as indicated by UV spectroscopy, suggesting that in double-stranded DNA, 5-methylcytosine sites may be protonated to a significant extent under physiological conditions.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ChemBioChem

ISSN

1439-4227

e-ISSN

1439-7633

Svazek periodika

19

Číslo periodika v rámci svazku

19

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

2088-2098

Kód UT WoS článku

000446429400012

EID výsledku v databázi Scopus

2-s2.0-85052403102